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186651

Sigma-Aldrich

18-Crown-6

greener alternative

99%

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Synonym(s):
1,4,7,10,13,16-Hexaoxacyclooctadecane
Empirical Formula (Hill Notation):
C12H24O6
CAS Number:
Molecular Weight:
264.32
Beilstein/REAXYS Number:
1619616
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

42-45 °C (lit.)

greener alternative category

SMILES string

O1CCOCCOCCOCCOCCOCC1

InChI

1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2

InChI key

XEZNGIUYQVAUSS-UHFFFAOYSA-N

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This Item
274984158402225487
18-Crown-6 99%

186651

18-Crown-6

18-Crown-6 ≥99.0%

274984

18-Crown-6

Dicyclohexano-18-crown-6 98%

158402

Dicyclohexano-18-crown-6

form

solid

form

solid

form

solid

form

solid

mp

42-45 °C (lit.)

mp

42-45 °C (lit.)

mp

-

mp

194 °C (dec.) (lit.)

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative product characteristics

-

greener alternative product characteristics

-

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative category

, Aligned

greener alternative category

-

greener alternative category

-

greener alternative category

, Aligned

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalysis. Find details here.

18-Crown-6 is the simplest crown ether that can be prepared by reacting triethylene glycol with triethylene glycol dichloride in the presence of potassium hydroxide as base.

Application

18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes.
Additive for greener etherification using KF-alumina.
Phase-transfer catalyst used in a chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide.
Can be useful as phase-transfer catalysts.

Other Notes

Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations).

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Description
Pricing

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Phase-transfer alkylation of heterocycles in the presence of 18-crown-6 and potassium tert-butoxide.
Guida WC and Mathre DJ
The Journal of Organic Chemistry, 45(16), 3172-3176 (1980)
Preparation and purification of 18-crown-6 [1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane].
Gokel GW, et al.
The Journal of Organic Chemistry, 39(16), 2445-2446 (1974)

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